Letters to an Almost Cowboy
by Madison Square
Summary: Racetrack mysteriously disappears! How will Jack (and the others) save him while trying to figure out some...romantic problems of his own? Complete
1. Default Chapter

Disclaimer:  Newsies does not belong to me.  []pout[]  I wish it did.  Oh, and I got the idea of using letters to tell the story from the book _Feeling Sorry for Celia_.  Sorry, can't remember who it's by, but it was a v. v. good book.  
  
  
==  
  
  
Letters to an Almost Cowboy  
  
  
==  
  
  
Madison Square  
  
  
==  
  
  
  
HEY!!!  HEY!!!!  OVER HERE!!!  DID YA FIND ME!!?? WELL, SINCE YOU'RE THE LEADER OF MANHATTAN, AND ALL, I FIGURED YOU'D WANT TO KNOW THAT I LEFT FOR THE TRACKS EARLY.  JUST SOME BUSINESS TO TAKE CARE OF.  WILL BUY PAPES AT CENTER IN BROOKLYN, BECAUSE IT IS CLOSER.  BE BACK BY DARK.

  
HAPPY SELLING,

RACETRACK  
  
  


  
  
Dear Mr. Francis Sullivan,

            Do _not_ worry.  Racetrack can take care of himself.  He says he'll be back by dark; he'll be back by dark.  Just freshen up, get your boys together, and get down to the distribution center.

            Look at Mush, smiling.  Even Skittery is smiling this morning as everyone washes up.  See?  Today is going to be a good day.  You wait and see.

            Stop Worrying.

Worry Free,

The Worry-Warts Ward  
  
  


  
  
Loverboy,

            Meeting Sarah for dinner after selling is just so romantic!  You're so handsome and romantic, aren't you?

            Wait.  What do you think you're doing?  Don't slurp your spaghetti.  Sarah won't like that.  And for goodness sakes!  Don't play with your food.  Look at her eyes.

            Do you see her looking at you?  So much love there, in her eyes.  You should do something more than just dinner.  A walk around the park, maybe?  And if it gets cold, you can offer her your jacket!  Well, assuming you buy one along the way.  How romantic.  Aren't you glad you thought of it?  Huh?

Lovingly,

The Young Romantics Association  
  
  


  
  
Muttonhead,

            What on Earth do you think you're doing?!  You're kissing her.  At night.  In the park.  There is no one else around.  This is the perfect opportunity to score, score, score!! But no.  You have to be all _nice_ about it.

            Maybe there's a reason, huh?  The _real_ reason you can't do anymore than kiss her?  You know why, Jack.  You know why.  You've looked at Mush a few times for a moment too long, haven't you?  Kept laughing at Racetrack's jokes long after the humor had gone?  Admired David for his smarts, then quickly for his eyes?

            So?  What'll it be, Jack?  Boys or girls?  You can't have both!*  Hurry up and choose!  Pick, pick, pick!!  Boys, girls, boys, girls?  And why are you still kissing Sarah?  Stop it.  If you don't choose _now_, she'll hate you for not telling her sooner.  She'll hate you, Jack.  

You.

Grudgingly,

Teen Angst Society  
  
  


  
  
Dear Cowboy,

            How awful.  You are an awful, awful person.  It was downright heartless when you said, "I'm sorry, but I don't have feelings for you when I kiss you."

            I'M SORRY?!  She's completely devastated!  Can't you tell?!  What if she decides to jump off the Brooklyn Bridge because her love life ended?  What if she becomes a nun?!  It'd all be your fault.  Not to mention that Davey is going to kill you.

            Yeah, that's right.  Just go about your business.  Pretend nothing happened.  Say 'Hi' to Skittery and Itey and Snitch.  Ask how the day was for Blink and Mush.  Check up on Specs and Dutchy.  Normal leader rounds.  But wait.

            There's one person not here.

            Racetrack.

            He's still missing.

            Bet that's your fault, too.

Think about it,

Guilty Consciences R'Us  
  


  
  
==  
  
  
  
I can't stop thinking about you.  But I know you already have someone, and the depression of knowing this fact is starting to get to me.  I fear I may have to jump off the Brooklyn Bridge.

Anonymous  
  
  


  
  
Boycow,

            You are probably wondering why we have spelled your name wrong.  There is a brilliant explanation for this.  We mixed up the letters so that in case this message was intercepted by someone, he or she would not be able to decipher to whom the message is directed.  Brilliant.

            Who could it be?  Huh?  Nice to find an anonymous note in your boycow hat right after you wake up.  Can't be Sarah, can it?  You broke up with her last night.  We wonder if 'anonymous' knows that you and Sarah are no longer a couple.  Who is it?  Think.

            Could it be Mush?  No, he's far too happy.

            Kid Blink?  Specs?  Dutchy?

Who is it, Jack?  Who is it?

Mysteriously,

Amateur Sleuths Association  
  
  


  
  
I'm kidding about the killing myself thing.

Anonymous  
  
  
  


  
Loverboy,

            Isn't it exciting!?  Your very own secret admirer!  Oh, your life is turning into such a drama!  First you break up with Sarah because you like to kiss boys, then this note!  Well, your secret love obviously has a sense of humor, if not a bit melodramatic.

            Can you wait for anymore of these letters?  We can't.

Love,

The Young Romantics Association  
  
  
  


  
Mr. Kelly/Sullivan,

            It has come to our attention that you lost one of your newsboys _yesterday_, and he is still missing today.  His name is Racetrack, yes?  Why haven't you found him yet?  Shouldn't you send someone after him?  Maybe he stayed in Brooklyn last night, and is selling over there today?  After all, Sheepshead _is_ in Brooklyn.

            Oh, that's great.  _Now_ you send someone to look for him.

            You say, "Swifty, run to Brooklyn for me, will ya?"  Swifty nods, only because you are his leader.

            "What for?"  Tell him, Jack.  But don't let any of your worry seep into your voice.  You're a leader, Jack.  You have to be strong.

            You say, "Ask Spot if he's seen Race."  

Good.  Your voice was friendly, but commanding.  Steady.  Just like a leader should be.

Swifty runs out the door.  He'll be back soon.

You did good, Cowboy.  You did good.

—Advice for Leaders Ltd.  
  
  
  


  
Cowboy,

            Swifty's back.  He'd holding a letter in his hands.  From Spot?  

            Uh oh.  His face doesn't seem so happy.  Probably not good news.

            What if Spot found Racetrack dead in an alley somewhere?  Race could be dead, Jack.  Gone.  Why else would Swifty look so down?  And Spot.  Surely he could have just asked Swifty to relay a message?

            But he felt the need to write it down.  Written words are easier to read than spoken words are heard, after all.  Must be bad.

            Swifty hands you the letter and then joins Skittery and Kid Blink and Mush in a game of poker.  It's not the same, though, because Racetrack isn't there to rub their losses in their faces.

            You read the letter and your heart skips a beat.

            Take a deep breath, Jack.

Brows Furrowed,

The Worry-Warts Ward  
  
  


  
  
jack,

            race not in Brooklyn.  not with me, anyway.  have a feeling he is in trouble.

            meet me at your end of the Bridge tomorrow, midnight.

—spot  
  


  
  
  
==  
  
  
  
End first chapter.  
  
  
  
*You could swing both ways, too, but for the purposes of this story, Jack is confused, so feels the need to make a quick decision, right then.

  
  
Read and Review!  Please?


	2. Chapter 2

Disclaimer on previous page.

Thanks to Frog, Gracie Jane, and Lefty for reviewing!  You guys get extra cookies!!

==   
  
  
Letters to an Almost Cowboy 

  
  
==  
  
  
Chapter Two  
  
  
==  
  
  
Madison Square  
  
  
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Mr. Kelly,

            GET UP!  You have to sell your papes.  Kloppman shouldn't have to yell at you more than once!  Shouldn't you be setting an example for the younger newsies?  That's right.  Move along.  You slowly trudge into the washroom to clean up a little.

            Move faster!  What are you, a snail?

            Don't you remember what you have to do today?  You're meeting Spot at your end of the bridge tonight.  Which means, get everything done _fast_.  And you can't go to Medda's tonight, or you'll drink and then you'll forget Spot and by doing so you've forgotten Race!  What kind of a leader would you be then?

            Skittery stands next to you while you are shaving and says, "Hey.  You okay?  You don't look too good."

            "I'm great, Skittery."  Are you _kidding_?  He'll see right through that.  You're supposed to keep everyone's hopes up because you're the leader.  But instead, your newsboys are cheering _you_ up.

            Itey pats you on the back and says, "Don't worry.  He's fine, I'm sure."

            You ignore him and walk back to the bunkroom to change.

            Wow, not much of a morning person, eh?

—Advice for Leaders Ltd.  
  


  
  
  
Glad that you ended it with Sarah.  But really, she's been whining and moping all day.  I would tell you who I am, but I can't bring up my courage to do so.

Love,

Anonymous  
  
  


  
  
Loverboy,

            Ooooh!  Another letter!  Don't you just wish your admirer would hurry up and reveal herself?  Don't you?  What a way to start the day, finding a love letter in your cowboy hat in the morning.

            People know something's up.  Bumlets just walked by and looked at you like you've grown horns.

            You know why, Jack?  Because you're smiling.  You haven't smiled like this since Racetrack disappeared.

XOXO,

The Young Romantics Association  
  
  


  
  
Boycow,

            Let's play a game.  See if you can figure out Anonymous' real identity before she reveals it!

            Clues:  smart enough to use the word 'anonymous,' knows Sarah, possibly more than you know her.

            Think, Boycow.  Do you know who it is?

Furtively,

Amateur Sleuths Association  
  
  
  


  
Jack,

            Amazing!  It's only Wednesday, and you've sold your papers in record time!  100 papes!  And that's just the morning edition!  Think how much you'll sell today!  You'll make at least three dollars by tonight.  Save up that money, Cowboy, and you're on your way to Santa Fe in no time.

Cheers,

Pepper Up Alliance  
  


  
  
  
You really shouldn't just leave your cowboy hat lying around.  Just anyone could steal it.  I bet these anonymous notes are starting to freak you out.  Don't worry, I don't stalk you.

Love,

An Almost Stranger  
  
  


  
Kelly,

            Can you believe it's already dark?  You walk around the streets of Manhattan, killing time before you have to meet Spot.  Can you imagine Spot doing the same thing?

            Obviously not.  _No one_ goes walking around Brooklyn at night alone.  Not unless said person can take real good care of himself.

            Well, Spot _can_ take really good care of himself.  So maybe he _is_ wandering around the dangerous streets of Brooklyn alone.  Maybe, he's even thinking of _you_ while you're thinking of him.  Maybe he's wandering the dangerous streets of Brooklyn thinking of you thinking of him!

            Oh, well, look at the time.  You walk over to the Bridge.  Spot is already there.

Inquisitively,

The Worry-Warts Ward  
  


  
  
  
Loverboy,

            He takes out a cigarette and a matchbox.  He doesn't try to offer you one, but that's probably because he is so worried about something.

            Aren't you surprised that you know him so well?  When he's worried, he narrows his eyes and wrinkles his nose from time to time.  And he smokes.  You can't think of another time when he smokes.

            He inhales deeply on the cigarette, then holds it over the rail between his thumb and forefinger.  His blue eyes focus on you and you drink in his appearance.  Gray cabbie hat, pink suspenders that were once red, slingshot, that mysterious key, his sharp blue eyes.  He says, "I'm gonna get straight to the point."

            You love the way he always gets straight to the point.

            "So talk," you say, and then you put your elbows on the rail next to him.

            "Racetrack's in trouble."

            You stiffen.

            "Yeah?"

            "Yeah," he affirms.  "I got these two notes from some guys about him.  Didn't say who they were."  He hands over two neatly folded pieces of paper.  You open the first one.  In big black letters it says, "WE'VE GOT RACETRACK."

            Before you can read the second note he puts his hand over yours and it sends tingles through your nerves.

            "Listen, Jack-y, I know you want to keep this problem in Manhattan, but the guys who have Racetrack thought he was one of my boys."  He pauses and inhales on his cigarette.  You notice his hand has not moved and you blush.

            "I want to help, Jack."  He removes his hand and the uncovered skin prickles with the lack of warmth.  He takes another drag on the smoking white stick.

            "Racetrack is a friend of mine.  A good friend."  A small smile graces his lips.  You decided not to read into the statement.

            You look over the river so he cannot see that you are uncomfortable.  "Of course you can help, Spot.  Just—I'll—I'll see what we have to do first."  You hold up the second unread letter as if to prove a point.  He nods, claps you on the shoulder with the same hand that once lay over yours, and says, "Let me know."  

Then he's gone.

            You really should be thinking of how to help Racetrack.  But all you can see is Spot's blue eyes.

            Can we say _crush_?

Telling it like it is,

The Young Romantics Association  
  
  


  
  
YOUR FRIEND RACETRACK OWES US QUITE A LOT OF MONEY.  $75, EXACTLY.  IF YOU EVER WANT TO SEE HIM AGAIN, WE SUGGEST YOU BRING THAT MONEY TO THE TIGER'S EYE PUB, BACK ROOM, MIDNIGHT, FRIDAY.  
  
  
  
==  
  
  
End Chapter Two


	3. Chapter 3

Disclaimer on first chapter.

Yay!  Repeat reviewed!  Thank you!!!!

==   
  
  
Letters to an Almost Cowboy 

  
  
==  
  
  
Chapter Three  
  
  
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Madison Square  
  
  
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Jack,

I know you are overwhelmed right now, trying to find Racetrack, but I can't wait anymore.  I want you to see me.  Don't you want to see me?  If you do, meet me outside of Tibby's Saturday at noon.  I hope I'll see you there.

Love,

An Almost Stranger  
  


  
  
  
Loverboy,

Finally!  Your admirer will reveal herself!  What do you think she looks like?  Brown hair and eyes, like Sarah?  Or something more exotic?  What do you think?  Aren't you excited?  We're practically bursting!  You'll meet her soon!

This could be the start of a beautiful relationship.

Anxiously,

The Young Romantics Association  
  
  


  
  
Mr. Kelly,

Stop swooning over love letters and get your butt in the washroom!  Don't you have more important things to worry about?  Like, say, SAVING RACETRACK?!  Yeah.  So how are you going to raise seventy-five dollars by tomorrow night?  _You_ certainly can't pay for all of it.  What about that Santa Fe money you keep locked up under your bed, huh?

Oh, of course not.  You would _never_ spend that money.  Selfish, much?

We've got an idea.  Ask everyone in this lodging house to donate just a dollar to the 'Give Race a Chance' Foundation.  There are about thirty boys in your lodging house, Jack.  That's thirty dollars a day.  Collect at night.  That way you have two nights to collect.  Sixty dollars.  You would still need fifteen.

Didn't Spot tell you he would help?  Go ask him, fool.

There, now that you've got that under control, what are you still doing in the washroom?!  Get your butt down to the lobby and roundup your boys so you can tell them your plan!  Go, go, go!

—Advice for Leaders, Ltd.

  
  
  
Cowboy!

Good speech!  The words just rolled off your tongue so naturally!

You gathered you boys in the lobby (and of course everyone stayed there throughout your entire speech.  You are an _amazing_ leader, you know?) and cleared your throat and everyone silenced like a flicker of flame disappearing.  Everyone looked at you with such hope and then you said:

"Boys, by now you all know that our good friend Racetrack is missing."  Murmurs of agreement here.  "Well, we know now that he is being held for random by a couple of thugs."  Cue the appreciative gasps.  "They want seventy-five dollars for him.  And we'll give it to them."

"Why don't we just hunt 'em down and soak 'em?" Boots asked.

"Because I don't want none of my boys to get hurt.  I'm not taking any chances.  They might have guns."  A few nods of consent.  Well handled, Cowboy!

"And so, in order to raise the money, I need each of you to give me a dollar a night."

"What?" an enraged Skittery screamed.

"Come on, Skitts.  They want the money tomorrow night.  You can spare a dollar a day for two days.  For Racetrack.  I mean, how many times has he lent you guys two bits of something 'cause you had a bad selling day?"

Skittery looked a bit ashamed and mumbled something, but he agreed.  Amazing, Cowboy.  With your persuasive powers of speech, we bet you could convince them to think left was right.

Cheers,

The Pepper-Uppers Alliance  
  
  


  
  
Dear Cowboy,

How much are _you_ donating to 'Give Race a Chance?'  Huh?  Two dollars?  Don't you have nearly ten dollars saved up under your bunk?  Why aren't you giving more money?  Leaving Spot to raise fifteen dollars?  You _know_ he doesn't want to have to involve his boys.

We bet _Spot_ would give his savings to help Racetrack.

Think on it,

Guilty Consciences R'Us  
  
  
  


  
Spot,

Need a little help with getting Racetrack back.  Meet me tomorrow at noon at my end of The Bridge.

—Cowboy  
  


  
  
  
==  
  
  
End Chapter Three   
  
Read and Review please!!!!!!


	4. Chapter 4

Disclaimer on first chapter.

==   
  
Letters to an Almost Cowboy   
  
==  
  
Chapter Four  
  
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Madison Square  
  
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Mr. Jack Kelly,  
We recently received a letter from Advice For Leaders Ltd. informing us that you have an incredible knack for planning. Escape plans, map plans, rescue plans, story plans, red plans, blue plans. All sorts of plans.  
We are here to tell you that you are legible for a subscription to our magazine "Plans Galore." Please reply by calling 1-800-PLAN456 (that is, if you have phone. Do you even know what a phone is?)  
Thank you for your time.  
  
Sincerely,  
1-800-PLAN456  


  
  
Kelly,  
Okay, so everyone donated their money yesterday. Will they today?  
You've already sold all your morning newspapers, and you decide to forego breakfast to save that dollar. Will everyone else?  
What if all this is for nothing? What if Racetrack is already dead and all this saved money goes to waste? What if Spot can't bring up the money? What if your plan doesn't work? What if—  
  
  
Cowboy,  
Relax. Take a deep breath. Pay no attention to the Worry Warts. Everything will be fine. Spot will come through with the money, after you tell him, of course. Everyone gave you a dollar last night, and they will tonight, too. You'll get enough money, Racetrack will be safe, everything will turn out beautifully.  
Relax.  
  
Yours,  
The Sit Down and Breathe Deeply Society  
  
  
Jack,  
_DING! DING! DING! _It's twelve o'clock! Noon! You're late, Jack! You're late! Run, run, run!!  
  
Promptly,  
Alarmed and Tardy  
  
  
Mr. Jack Kelly,  
Quick, think of anything you can to apologize to Spot for being late.  
"You're late, Cowboy," he says. He's smoking again, and he drapes his figure over the rail of the bridge. He and the steel bars are about the same in thickness.  
"Sorry, Spot," you say, a little breathless because you had to run to the Bridge. Now talk to him about Racetrack. Don't stall, it makes you look weak. You open your mouth to say something, but he beats you to it.  
"I read that letter, you know; I know you want my help." He is calm and collected, like you _should_ be.  
"Yeah," you agree. "We need a little more money."  
"I can get you ten dollars," he replies swiftly. "No more. That's all I've got."  
"That's all you've got?" Great, Kelly, now you sound like a parrot. _Squawk! Squawk! That's all you've got! Squawk!_ Get a hold of yourself. Tell him that ten dollars is enough. Ask him why he can't conjure up more money.  
"I don't want to involve my boys, Kelly," he huffs. "This is personal." He inhales some smoke. It is like he can read your mind.  
"Ten bucks is enough," you say, to satisfy him. Jack, when are you going to grow a backbone? You should have demanded another five dollars. Where are you going to get that money?  
  
—Advice For Leaders Ltd.  
  
  
Cowboy,  
Astounding! Awe-inspiring! You will be a great President one day, Mr. Kelly. After receiving the money Spot promised you, a trip to the little box under your bed proved that you are very self-sacrificing. You are donating _five more dollars_ to the 'Give Race a Change' Foundation! We are so proud of you! To reward your act of leadership generosity, we are saving a space for you at your next formal dinner.  
  
Sincerely,  
The Society of Future Leaders  
  
  
Jack,  
_DING! DING! DING!_ It's 6:30 p.m! Time for dinner! Time for a game of cards! Hurry, hurry, hurry!!!   
  
The Clock is Ticking,  
Alarmed and Tardy  
  


Kelly,  
It's amazing! It's wonderful! It's fate! Everyone has given you the proper amount of money! You now have seventy-five dollars! You plan worked! You are a genius! Brilliant! Extraordinary!!!  
  
Cheers,  
The Pepper-Uppers Alliance  


  
  
Cowboy,  
Shady place, isn't it? You walk into the Tiger's Eye Pub. It is 11:57 p.m. Immediately the stench of cheap alcohol and days old cigarette smoke fills you. The fellow at the bar glares and growls at you as you pass. Just ignore him, Kelly. Get the back room. Give them the money. Save Racetrack. That's all you have to do.  
  
—Advice for Leaders Ltd.  
  
  
Kelly,  
We should be calling you SuperCowboy! The way you swooped into the room, intent on saving your friend, astounded us. Whoosh! Smack! Yee-Haw!  
"I've got your money," you said to the thugs, reveling in how they flinched at your words. "Now let go of Racetrack."  
And then they tried to persuade you to give the money to them first, that they had Racetrack outside, and they would bring him in as soon as they got the money. But you were too smart. You demanded that they gave Racetrack back first.  
Grudgingly they had nodded to each other, and the smallest one swaggered out the back door. He came a few seconds later with Racetrack, a little battered, but otherwise alive. He smiled at you slightly when he limped in; his lip was cut so he couldn't grin any larger.  
"I knew you'd come through," he said, his voice scratchy.  
"Of course, Racetrack."  
Score one for you, SuperCowboy. You are welcome to join our ranks anytime.  
Heroically,  
Superheroes of New York, Inc.  
  
  
Dear Jack,  
You've saved Racetrack! Congratulations! I'm glad he's okay. I'm glad that _you're_ okay. I hope nothing like this ever happens again. I hate it when you're worried.  
You _are_ going to Tibby's tomorrow at noon, right?  
  
Love,  
Stranger Whom You Will Possibly Meet Tomorrow.  
  
==  
  
End Chapter 4  
  
[A/N]:  
  
Thank you to LeftyHiggins and Ccatt for reviewing! Sorry it took so long for me to write, but I was having a major writing block with this story. But now that writing block has transferred to See Spot Run. Argh.  
  
Read and Review please!!!!!!  
  



	5. Epilogue

Disclaimer on first chapter.

==   
  
Letters to an Almost Cowboy   
  
==  
  
Epilogue  
  
==  
  
Madison Square  
  
==  
  
HEY!!! HEY! OVER HERE!! LOOK OVER HERE, COWBOY!! YOU POSSIBLY NOTICED THAT I AM NOT IN THE LODGING HOUSE, AGAIN. DON'T WORRY. AT SHEEPSHEAD IN BROOKLYN. DON'T WORRY. NO TROUBLES TODAY. BE BACK BY DINNER, REALLY.  
  
HAPPY SELLING,  
RACETRACK  
  
P.S. DON'T WORRY.

  
  
jack, 

going to sheepshead with racetrack. making sure nothing happens to that idiot. why are all your boys so stupid? just saw walkin' mouth skipping around on the Bridge. does he want to get killed? jack, talk to your boys about using their brains.  
  
—spot

  
  
Loveryboy,  
Are you surprised? Bewildered? Star struck? We are. When you walked up to Tibby's, cheeks red and heart beating frantically, you weren't sure if you really wanted to go in or not. But you made the right choice, and you opened the door.  
You were hoping for maybe a pretty girl to be sitting in an empty booth, smiling as you walked in and fluttering her eyelashes. You knew it wouldn't be a girl, though, didn't you? Girls aren't allowed in the Lodging House. A girl couldn't have written those wonderful letters. You knew this, and yet you hoped.  
How sweet.  
When you stepped into the restaurant, the world didn't stop. People were talking, glasses were clanking. Everywhere there was noise, movement, laughter. Except in one booth in the corner.   
There was Dave, looking at you with hope and affection, and you weren't surprised.  
The next move is yours, Cowboy.  
  
With Anticipation,  
The Young Romantics Association   
  
==   
  
End Epilogue  
  
End Fic  
  
[A/N]:  
  
ThanQ to anyone who stuck with me through this fic! Haha. 

::hands Strawberry Shake a strawberry milkshake:: Thanx for reviewing!  
How come everyone knew it was DAVID? Haha. Just kidding. Who else would it be?  
  
Read and Review please!!!!!!


End file.
